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Synthesis 1995; 1995(9): 1179-1182
DOI: 10.1055/s-1995-4433
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Carbamoyloxa-Bridged Cyclophanes: Macrocyclization by Double Transesterification of Dimethyl m-Xylylenedicarbamate with α,ω-Dihydroxy Compounds

Shin Irie, Makoto Yamamoto* , Keiki Kishikawa, Shigeo Kohmoto, Kazutoshi Yamada
  • *Department of Materials Science, Faculty of Engineering, Chiba University, 263, Japan, Fax +81(43)2903039
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Publication Date:
31 December 2000 (online)

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A series of macro-sized (16-24-membered) carbamoyloxa-bridged cyclophanes 3a-k was prepared by sequential inter- and intramolecular transesterifications of dimethyl m-xylylenedicarbamate with α,ω-dihydroxy compounds 2a-k in good yields (15-74%) without the use of high-dilution techniques. Precursor 4 with lower reactivity cyclized selectively to the desired 1:1 coupling products catalyzed by SnCl2. The conformationally rigid m-xylylene template restricted the location of the two carbamoyloxa-bridges, which resulted in moderate binding affinities to the potassium cation. The binding ability of these carbamoyloxa-bridged cyclophanes was evaluated by the extraction study of aqueous alkali metal picrates, (log K a=3.6-4.0) with the formation of a 1:1 complex.

cyclophane - macrocyclization - transesterification - carbamate - potassium cation - heteromacrocyclic receptor